22596-62-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Phenyl-propyl)-acetamide is used as an analgesic and antipyretic agent for its ability to relieve mild to moderate pain and reduce fever. Its efficacy in managing pain and fever, coupled with a mild and generally well-tolerated side effect profile when used at recommended doses, makes it a popular choice in over-the-counter and prescription medications.

InChI:InChI=1/C11H15NO/c1-9(8-12-10(2)13)11-6-4-3-5-7-11/h3-7,9H,8H2,1-2H3,(H,12,13)

Upstream product

• 692-33-1 N-allylacetamide 
• 71-43-2 benzene 
• 582-22-9 2-phenylpropylamine 
• 72-89-9 acetylcoenzyme A 
• 108-05-4 vinyl acetate 
• 141-78-6 ethyl acetate 
• 20780-53-4 (R)-Styrene oxide 
• 108-24-7 acetic anhydride 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 98-86-2 acetophenone 
• 34713-70-7 2-Phenylpropanal 
• 20388-87-8 rac-β-methylphenethylamine hydrochloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 59261-37-9 1,4-dimethyl-3,4-dihydroisoquinoline 
• 1721-95-5 1,4-Dimethyl-isochinolin 
• 162662-88-6 2-(2-phenylpropyl)-1H-isoindole-1,3(2H)-dione 
• 71825-43-9 N-[2-(4-nitrophenyl)propyl]acetamide 

Relevant academic research and scientific papers

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

Quinazoline derivatives and its preparation method and application

The invention relates to quinazoline derivatives and its preparation method and application. The quinazoline derivatives with The structural formula, the quinazoline derivative to gefitinib for the positive control, the result shows that compared with the gefitinib has good activity; and lead compound OTS514 compared, equivalent activity, PBK/TOPK inhibitors for further transformation and the discovery of new anti-tumor medicine phenological shopping has higher learning with the reference value. The invention also provides a preparation method of the quinazoline derivatives and the preparation of PBK/TOPK inhibitor and an anticancer drug.

Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis

A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).

Mechanistic and structural analysis of Drosophila melanogaster arylalkylamine N-acetyltransferases

(Chemical Equation Presented). Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N-acetylation of arylalkylamines is a critical step in Drosophila melanogaster for the inactivation of the bioactive amines and the sclerotization of the cuticle. Two AANAT variants (AANATA and AANATB) have been identified in D. melanogaster , in which AANATA differs from AANATB by the truncation of 35 amino acids from the N-terminus. We have expressed and purified both D. melanogaster AANAT variants (AANATA and AANATB) in Escherichia coli and used the purified enzymes to demonstrate that this N-terminal truncation does not affect the activity of the enzyme. Subsequent characterization of the kinetic and chemical mechanism of AANATA identified an ordered sequential mechanism, with acetyl-CoA binding first, followed by tyramine. We used a combination of pH-activity profiling and site-directed mutagenesis to study prospective residues believed to function in AANATA catalysis. These data led to an assignment of Glu-47 as the general base in catalysis with an apparent pKa of 7.0. Using the data generated for the kinetic mechanism, structure-function relationships, pH-rate profiles, and site-directed mutagenesis, we propose a chemical mechanism for AANATA.

Silica-supported polyphosphoric acid in the synthesis of 4-substituted tetrahydroisoquinoline derivatives

We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4- tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylation of the obtained amines with different acid chlorides or sulfochlorides. We compared the cyclisation step using conventional (milieu of acetictrifluoracetic acid = 4:1) and solid supported reagents (SiO2/PPA), as recovered, regenerated and reused without loss of its activity catalyst. We found that in comparison to conventional methods, the yields of the reaction are greater and the reaction time is shorter.

Potential antitumor agents. 13. 4 Methyl 5 amino 1 formylisoquinoline thiosemicarbazone

4 Methyl 5 amino 1 formylisoquinoline thiosemicarbazone has been synthesized in an attempt to obtain (a) high affinity for the target enzyme ribonucleotide reductase, (b) water solubility as an acid salt of the amine, (c) steric protection of the amino group from in vivo acetylation, and (d) insensitivity to O glucuronidation, a major factor in inactivity in man of 5 hydroxy 2 formylpyridine thiosemicarbazone. The synthesis was achieved by nitration of 1,4 dimethylisoquinoline at the 5 position followed by selective oxidation with selenium dioxide to the corresponding 1 carboxaldehyde. The aldehyde group was protected by conversion to the cyclic ethylene acetal which was then catalytically reduced to produce the 5 amino derivative. Reaction with thiosemicarbazide in the presence of hydrochloric acid yielded the desired derivative. This agent was found to be an effective antineoplastic agent in mice bearing Sarcoma 180 ascites cells and at the maximum effective daily dose of 10 mg/kg increased the average survival of animals threefold over untreated tumor bearing controls.